(2S,3S,4S,5R,6S)-6-(5-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167772
• Molecular Formular: C13H14O10
• Molecular Mass: 330.24426
• Monoisotopic Mass: 330.05869665
• SMILES: c1c(c(cc(c1)C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1cc(ccc1O)C(=O)O
• InChI: InChI=1S/C13H14O10/c14-5-2-1-4(11(18)19)3-6(5)22-13-9(17)7(15)8(16)10(23-13)12(20)21/h1-3,7-10,13-17H,(H,18,19)(H,20,21)/t7-,8-,9+,10-,13+/m0/s1
• InChIKey: CXNFDJSOAJNKSU-CDHFTJPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(5-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(5-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-Carboxy-2-hydroxyphenyl β-D-Glucopyranosiduronic Acid; 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 953037-17-7
• PubChem SID: 162261905
• PubChem CID: 71316220

CALCULATED PROPERTIES

• Acid pKa: 2.749706
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.9625707
• LogD (pH = 7.4): -7.4908104
• Log P: -0.92409545
• Molar Refractivity: 69.2878 cm^3
• Polarizability: 27.788319 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: >165°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D451685

3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide is a metabolite of Protocatechuic aldehyde, a major bioactive phenolic acid in the roots of Salvia miltiorrhiza.

REFERENCES

• Rao, S., et al.: J. Biotechnol., 76, 137 (2000)
• Zhang, Y., et al.: Drug Metab. Dispos., 32, 752 (2000)
• Pan, J., et al.: J. Pharm. Biomed. Anal., 42, 565 (2000)